


Helping Friends

by BunniesAndBooks



Series: The Christmas Calendar [2]
Category: Glee
Genre: Blow Jobs, F/M, Multiple Orgasms, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2014-12-25
Updated: 2014-12-25
Packaged: 2018-03-03 11:18:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,926
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2849021
Author URL: https://archiveofourown.org/users/BunniesAndBooks/pseuds/BunniesAndBooks
Summary: <blockquote class="userstuff">
              <p>Day 2. Kurt/Brittany<br/>Brittany thinks she might be gay so she convinces Kurt to have fluffy, awkward sex with her 'just to make sure.'</p>
            </blockquote>





	Helping Friends

”Hey, Kurt!” Kurt heard someone yell behind him, and while this would usually freak him out as it tended to be one of his bullies calling out for him most of the time, this time he could tell it was just Brittany. So he merely turned around and waited for the ditzy cheerleader to catch up to him.

”Hi Britt, what's up?” he asked his friend, allowing her to grab his gloved hand and swing it in the air between them as they continued walking out of the school and into the freezing cold.

”Well, Kurtie, I was talking to Santana and I think I might be gay. Did you know that dolphins are just gay sharks?”

Kurt had gotten used to being somewhat confused by Brittany’s little comments, but it never ceased to amaze him. ”Umm, okay?”

”So, I was thinking, since you're capital G gay, can I have sex with you so I can be sure? Lord Tubbington thought I was just being dramatic when I told him.”

At the first mention of sex Kurt's mind blanked, but when he fully processed what the blonde had said he stopped walking and just looked at her with her mouth hanging open. Brittany though kept going until their linked hands brought her to a stop and she turned back to Kurt, looking confused. ”Britt, w-what?”

”What, what?” She asked tilting her head to the side.

”W-why do you want to- to have... s-sex, with me if you think you're gay? Wouldn't that defeat the purpose?” He couldn't believe he was having this conversation.

“Oh, I don't want to get married to you, I just want to have sex with you.” Wait, what? What the- “And why would we be defeated if we got married?” Brittany asked looking at him with her head tilted, horribly confused from his words.

“Never mind,” Kurt responded, closing his eyes in slight frustration. “But why, Brittany, do you want to have sex with me?”

“Like I said, I want to know if I'm a dolphin too, and the only way I'll know that is if we sleep together. Duh.”

“Oh Britt-Britt, I don't think...” Kurt started, only to see the blondes eyes growing watery at his words and her lips beginning to tremble. Running his hand over his face and chanting internally at himself that _he shouldn't do this, it was a stupid idea and he was a fool for even considering it_...

“Yeah, sure Brittany,” he sighed heavily, “sure, I'll sleep with you, though I'm not sure it will work.”

“Why do everyone keep saying they want to sleep when I ask if they want to have sex?” Brittany asked him, her face yet again showing confusion. And while this normally would make Kurt think 'adorable and sweet', this time he only landed with 'oh sweet Madonna'. 

What had he gotten himself into?

*

“Are you sure about this?” Kurt asked for about the twentieth time since leaving McKinley. They were now sitting side by side on Brittany's bed, Brittany holding on to one of Kurt's hands with both of hers and petting it. “You can change your mind, you know,” he reminded her, somewhat pleading with her to change her mind, but knowing deep down she wouldn't. “I won't mind.”

“I'm sure,” Brittany cooed, stroking the pad of his thumb fascinated by how soft they were. “I want to know if I'm gay or not. And sex is fun, plus your hands are really soft, like baby hands, and I really want you to finger me right now,” she finished bluntly, looking into his eyes.

Kurt on his end blushed a furious red, eyes closing on themselves as his breath caught in his throat. His heart began beating horribly fast and he felt slightly panicky; it was all happening way too fast.

“Umm... yeah... hmm... um...” Kurt fidgeted. “Can't we kiss a little bit first?” At least he was familiar with that, the stark reminder of his 'butch period' clear in his mind. Maybe if they kissed he could get his head around what was happening.

“Sure, you're a really good kisser Kurtie.” 

And apparently that was that because suddenly Kurt found himself with a lap full of Brittany, her tongue delving into his mouth and pressing against his teeth.

“Whoa!” Kurt exclaimed, breaking away and grabbing a hold of the girl straddling his thighs. “I was thinking more like... um... _calm_ kisses,” he muttered at a loss for better words. “And then maybe we can work up to kisses like _that_.”

Brittany only rolled her eyes. “Okay, okay. But usually when guys are gonna have sex with me they want me to kiss them like that, so... Oh!” she cried out with wide eyes when she thought of something, “but by then they have mostly licked my armpits first, 'cause it gets me totally hot, and then they kiss me like that. Do you want to lick my armpits first too?”

Oh holy Madonna... Kurt had wholly forgotten about that little tidbit about the blonde girl. But there was no way, _no way_ , he was ever, _ever_ , going to lick her armpits. “No honey... no. I think I'm good,” he said, scrunching his face up at the very thought.

“Suit yourself, it's really sexy,” she shrugged, going back to kissing him. Though this time with her mouth closed. Her hands framed his jaws, her thumbs moving against his cheeks calmly as she moved her lips against his.

Kurt's eyes fell shut, and he brought his hands up to her waist, holding her gently as he cautiously kissed her back, trying so bad to get into it. Though, much like last time, he couldn't quite get past the feeling of it being _wrong_.

But he had promised the ditzy blonde to do this, and he wasn't going to back down on a promise. Especially not on someone as naive and sweet as Brittany.

He let one of his hands travel up the backside of her cheerio top and up to her ponytail, his deft fingers working the hair loose as he tilted his head and kissed Brittany a little bit deeper than before. Soon her long hair was framing her face, strands of it falling against Kurt himself and reminding him yet again that he was doing this with _Brittany_ of all people.

Taking a deep and calming breath through his nose Kurt decided that if he was actually going to go through with this he might as well try to do it as good as possible for the tall girl. Though he might not know much – or anything really – about the female body, how hard could it possibly be to make one fall apart?

So, on the count of three Kurt finally opened his mouth and carefully licked over Brittany's cherry flavored lips, soon letting his tongue tentatively enter her own very much enthusiastic mouth, their tongues delving together and exploring. And while he may not be that interested in Brittany there was something about kissing somebody like this that got to him; it was intimate and new, surprisingly mind-blowing and to put it frankly – rather _amazing_. He could get used to kissing somebody like this.

Allowing his hands to bury themselves into Brittany's blonde locks he cautiously canted her head, finding a new angle that made their lips slant together better, one where their noses wouldn't be bumping into the other's constantly like they had before.

He could feel fingers dancing across his body, nimble fingertips tracing circles over his neck and shoulders, skimming over his arms and torso, teasingly plucking at his nipples and making him shudder from the titillating sparks that elicited. Then suddenly there was a palm pressing down against his most private part of his body, and despite still being completely and utterly soft, he gasped. This was the very first time he'd had anybody apart from himself ever touch him there, and it was overwhelming to say the least.

“Brittany,” he whispered biting his lip. “Um, not to complain or anything... but can we... lay down or something?” Anything to get her to remove her hand for a few minutes so he could calm his racing heart.

She only nodded her head, going back to kissing him as she left his lap and pulled him down above her on the bed. And this was much better, Kurt found. Now her hands were occupied with petting over his back, and he felt much more in control of the situation.

Of course that was when she let her hands fall down to his own, grabbing them and leading them up to her breast, making them cup around her, _squeezing_ her.

So much for being in control of things.

But Kurt wasn't going to say anything; this was just two bumps of flesh after all. Nothing dangerous. So he might not be attracted to the whole boob thing, but it didn't mean he was scared to touch them or anything. Didn't mean he was disgusted by them.

So he played with them. Awkwardly, might he add. It was obvious that he had squeezed them too hard one or two times when Brittany whined through clenched teeth, but he had also made her moan against his lips a few times, so he counted that as a win, albeit a small one.

Eventually though he allowed one of his hands to fall away while the other was busy playing with one of her nipples through the red cloth of her Cheerio top, his fingers skimming up her soft arm to her neck where he palmed her jaw, his thumb stroking over the skin on her cheek as he kissed her softly.

It wasn't long after that that Brittany pushed him away though. At first he was confused by her actions, but it all became _very_ clear when she reached down for the hem of her shirt and in one quick move removed it from her body. He blushed watching her just sitting there before him, half naked of all things, in only her bra and her skirt.

He knew from countless stories from Puck and the other guys that the girl hardly ever wore panties, something which made him blush even harder when he remembered _that_ particular fact.

And then he blushed a little harder still when the blonde reached for his own shirt and began unbuttoning that too, soon removing it from his body and revealing just how far his blush had spread. He removed his white wife beater on his own though, needing to keep some sort of semblance of things.

The next thing he knew he was pushed down on the bed, Brittany laying splayed above him with her almost bare breasts pressed against his own skin, her teeth nibbling into his pale throat. He couldn't help but keen though, whatever she was doing to his skin felt impossibly good, and he grabbed hold of her waist to keep her there, just for a moment longer.

Soaking in the feeling of having his neck ravished like this Kurt forgot himself momentarily; his hands feeling their way down her soft flesh down to her still covered ass, grabbing it in his palms and pressing her closer to him, to his slowly awakening member.

She groaned against his neck in return and soon began grinding herself down against him as she sucked a bit of his skin into her mouth, lapping at his marked flesh with a soothing tongue.

Suddenly remembering something his step-brother had mentioned in passing about girls needing to be prepared before one could have 'proper sex' with them, that they needed to be wet or they would get cranky and scary, Kurt slowly and hesitatingly brought one of his hands from Brittany's supple ass between their two bodies. Hitching the girls short skirt up (which was very awkward considering how closely the two were pressed together at the moment) and slowly pressed his fingers against something he had never encountered before in his life, something he never had thought he ever _would_.

No need for it to be said, but Kurt had no idea in hell what he was doing at the moment. All of his ministrations were based on was the one fleeting comment about a girl needing to be 'wet' before you could have sex with them. But how did one get them there, and what was that _thing_ pressing against his wrist above her- was it a slit it was called?

So mostly Kurt just allowed his fingers to trace all over her sex, searching and exploring for any indication that what he was doing was working. But Brittany didn't make any sound apart from the occasional slurp when she attacked a new spot of his neck.

On a side note, he was going to be completely back and blue tomorrow wasn't he? Great, and how exactly was he going to explain that to his father? And which of his scarves would he use to cover everything up with?

Thankfully Brittany seemed to catch on to his situation, and taking hold of his hand she brought one of his fingers against her sex, and pressed it inside her.

She was tight, impossibly tight. No wonder guys liked sleeping with girls if they felt this tight just around his finger; just imagine what it would feel like having this stretched around his dick. But maybe it was just Brittany that was this tight?

Kurt still knew naught about how to get a girl wet, but he figured that since Brittany had made sure to press him inside her she wanted him to play with her there. So he brought his finger back out and slowly pressed it back inside, feeling it slide just a little bit easier that before. In and out, in and out, in and out. With each press in Brittany was a tad slicker, a tad more open and willing to allow him in. At last Kurt felt confident enough that this might actually work out in the end.

“Two. Now, give me two,” he could hear the blonde murmur into his collarbone where she had begun marking him. His neck was probably out of unblemished skin now then. Oh his skin regimen would hate him after this wouldn't it?

But anyway, she'd said two. How could that possibly work? She was still so incredibly tight, and she was no where wet enough, but she should know her own body good enough for this shouldn't she?

Slowly and carefully Kurt introduced a second finger to her hole, easing it inside gently, an lo and behold she sucked the digit in almost greedily. He may be fitting snugly inside her, but he fit after all.

So he began thrusting the two fingers inside her now – all the while feeling her opening up around him, slowly, slowly. His other hand was playing with her hair, going back and forth between twiddling it around his fingers and idly petting it. 

She had such smooth and soft hair, he should get her to tell him how she treated it...

“Clit,” he hear Brittany panting against him. “You should rub my clit.”

“What's a clit?” Kurt asked confusedly. Female anatomy was so not his strong suit.

She sighed and once again reached down for his hand, taking his thumb and making him press against this little nub that made her gasp and clench her other hand into his shoulder.

'That was the _thing_ he had felt earlier!' Kurt thought excitedly, but moderately so, it wasn't like he was actually getting into this. No sir, no.

But he pressed against it, rolling it back and forth with his thumb and listening to every little gasp and breath Brittany gave out because of it. His fingers inside her had stilled while he first found the little nub, the _clit_ , but now he felt confident enough to attempt to do both things simultaneously.

While a little, well, _awkward_ , he somehow managed to keep up with both things, and it wasn't long until he felt her clench around him, and wasn't that an experience, realizing that you had made somebody _come_.

Knowing oneself was the cause of that? It was thrilling. And a tiny bit arousing.

Easing his fingers out of the girl Kurt pressed a chaste kiss against the top of her head, the only piece of her he could reach where she was slumped down on top of him, still panting raggedly.

But it wasn't long before she was sitting up on top of him, smiling hugely down at him.

“Thanks for fingering me,” she said sweetly, leaning down and kissing his cheek. “Most guys doesn't, and when they do they hardly ever make me come.” _That_ threw Kurt for a loop; he had managed to do something most other – overwhelmingly _straight_ – guys wouldn't? Couldn't? Wow... 

“I'm gonna blow you now,” Brittany announced abruptly and out of the blue, reaching down for his jeans and popping the button without preamble. Within seconds his jeans and underwear were shimmied down and away, and he now lay completely bare before the blonde girl. Luckily he was still rather out of it – stuck on the topic of both being able to get Brittany off, but also of the blatant information that he was going to get his first blowjob – to fully realize that he was utterly _naked_ , before a girl no less, so he had no chance of building up any of the panic he normally would when it came to being naked publicly.

No, instead there was suddenly a wet, warm heat surrounding his very most personal part of his body. Warm, smooth hands were gripping the base confidently as a wet tongue was lapping around his crown, and before long Kurt could feel Brittany's mouth closing around him, _swallowing_ him.

Crying out from the abrupt onslaught of pleasure Kurt – completely out of control – bucked his hips up, seeking more of that wet warmth.

He could hear Brittany cough and sputter below him, and he mumbled out a litany of 'I'm so sorry's' behind the hands he had hidden behind, ashamed of his body's reaction.

“It's okay Kurt,” Brittany said, bringing Kurt's hands away from his face and looking into his eyes with her own big, blue eyes. They were filled with tears though, and it just made Kurt feel even more guilty so he closed his eyes again, hiding from her stare. “Hey, it's okay,” he heard her say, cupping his cheek with her palm and kissing his nose. “Don't be sad dolphin, all boy's do that during their first blowjob, it's because their penises are so happy to see me. Okay?”

And somehow, her silly explanation made Kurt feel just a tiny bit better, and he giggled quietly at her words before opening his eyes. “I'm really sorry though. I didn't mean to...”

“I know,” was the only thing she said before leaning down and claiming his lips.

They stayed pressed together for a while longer, just kissing each other calmly, somewhat chastely. But then Brittany broke away and started searching through her bedside drawer.

“Santana told me I always needed to use one of these,” she said, holding up a condom. “I don't know why though, she didn't explain that. But I trust her, so I'm going to put it on you, okay?”

Kurt nodded. Things were getting very real right now. He was about to loose his virginity in just a few short moments – if he hadn't already with that botched blowjob – but surprisingly, he was rather okay with it. He knew almost nobody had a perfect first time, or were with that perfect person, but he had Brittany, and he liked her, trusted her. She would be a good person to loose his virginity to.

He moaned lowly feeling her roll the rubber down his length, and before he knew what was happening she was sinking herself down on top of him, steadying herself against his chest as she did.

As he had expected earlier she was tight around him, snug like a glove as she was filled up entirely by himself, and the experience was far better than he had thought it would be. If this is what it felt like being on top – even when the bottom was a girl, and she was technically the one on top – Kurt couldn't think about ever giving it up.

He hurried to grab hold of her skirt covered hips when she struggled to start a rhythm of bouncing up and down on him, helping her by lifting her up before dropping her down. But it wasn't long before his arms grew tired of the task and he gently, but hurriedly, flipped them so he was laying on top of her. She quickly wound her long legs around his   
back, pressing him in and closer, whining when he wasn't moving quickly enough for her tastes.

He lifted her skirt out of the way, and eased himself down over her so he could take her bottom lip between his and nibble on it. Only then did he pick up the pace, pushing himself in faster, harder... deeper.

It was a struggle to trust himself into her and kissing her at the same time, so he broke his lips away and buried himself down into her neck, mouthing at the skin there as he continued to pound into her carefully but quickly.

Kurt could already feel himself close to coming, and wanting – no, _needing_ – Brittany to come first, Kurt took advantage of a little trick she had taught him earlier and brought two fingers down to her clit and started furiously rubbing at it. Only seconds after could he feel her begin to shake and twitch as she clamped down on him, milking him for all he was worth, and he came into the condom, shooting rope after rope of milky white cum into the rubber.

Slumping down on her Kurt kissed her sweat soaked skin as he eased himself out of her, before getting out of the bed and throwing the soaked and tied up condom away before returning to her with a washcloth.

“You were always my favorite boyfriend, Kurtie,” Brittany mumbled tiredly as he cleaned her up, and she was asleep before he had returned from placing the soiled cloth into the laundry.

“And you will always be my favorite girlfriend Britt-Britt,” Kurt whispers quietly as he presses a kiss to her forehead before getting dressed and leaving her house, realizing the time and knowing he is late for dinner at home.

*

“I forgot to ask you yesterday, Britt-Britt, but did you figure out if you were gay or not?” Kurt asked the day after as the two left the choir room, Brittany once again swinging their joined hands between them.

“I don't know,” she responded cheerily. “Maybe. I don't really remember how I felt when we had had our orgasms, because I fell asleep so quickly,” she explained, shrugging her shoulders.

“Well, maybe you should go ask Santana to help you the next time,” Kurt told her, hoping she would take his advice. While it had been a good experience that he had enjoyed he wasn't sure he wanted a repeat performance of it.

“Yeah, maybe. She's really smart. She always teaches me new stuff, so maybe she will know. Thank you Kurtie!” she exclaimed, hugging him tightly to her.

Kurt could only chuckle at the girl's antics. “You're so welcome Britt-Britt.”


End file.
